Benzenesulfonyl chloride → MLS003115187

HRID 844407Notes

Reaction equation

HRID 844407 reaction equation
[C:1](=[N:14][NH2:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)C>[C:2]1([C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:14][NH:15][S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 79304Diphenylmethylidenehydrazine

Product 1

HCID 315047MLS003115187

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A four neck flask (2 liters) equipped with a thermometer, a reflux condenser and a stirrer was charged with 78.4 g (0.4 mol) of benzophenone hydrazone, 64.6 g (0.64 mol) of triethylamine and 1 liter of ether, and 105.6 g (0.6 mol) of benzenesulfonic acid chloride was dropwise added thereto in one hour while stirring at room temperature and then heated under reflux for 72 hours. The reaction liquid was cooled down to 20° C. and then washed (separated) twice with 500 ml of deionized water. The ether layer was dried over anhydrous magnesium sulfate and filtered off, and then the mother liquid was concentrated by means of a rotary evaporator to obtain reddish yellow crystal. This crude crystal was added to 1 liter of diethyl ether and heated under reflux for 30 minutes, and then the crystal was filtered off at 30° C. This was dried under reduced pressure to thereby obtain white crystal.

Workup

  1. customA four neck flask (2 liters) equipped with a thermometer, a reflux condenser and a stirrer
  2. additionwas dropwise added
  3. temperatureheated
  4. temperatureunder reflux for 72 hours
  5. customThe reaction liquid
  6. temperaturewas cooled down to 20° C.
  7. washwashed
  8. custom(separated) twice with 500 ml of deionized water
  9. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltered off
  11. concentrationthe mother liquid was concentrated by means of a rotary evaporator
  12. customto obtain reddish yellow crystal
  13. temperatureheated
  14. temperatureunder reflux for 30 minutes
  15. filtrationthe crystal was filtered off at 30° C
  16. customThis was dried under reduced pressure
  17. customto thereby obtain white crystal

Sources & evidence

ORD record
ord-0431a1576c534fa5bd286b44b8f4dad8
Source dataset
uspto-grants-2002_04
Patent number
US06380288B1

Reaction notes

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